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PrakashGrama-5761 asked JeffYang-MSFT edited

Exception to Outlook Rule is not working

I have set a rule to delay all outgoing emails by 1 minute but have set an exception that if it is assigned to any Category, it should be sent out immediately. When I do not assign a Category, the mails are going out after the 1-minute delay. But when I assign it a Category, instead of being sent immediately, it gets stuck in Outbox! And if I edit it after that and remove the Category assignment, it doesn't help and is still stuck. I have tried deleting the rule and recreating it but it still doesn't work.

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Hi @PrakashGrama-5761,
Just checking in to see if above information was helpful. If you have any further updates on this issue, please feel free to post back.

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JeffYang-MSFT answered JeffYang-MSFT commented

Hi @PrakashGrama-5761,

Welcome to our forum!

According to your description, sounds like that the Outlook Rule you set is reasonable, and the stuck issue should have nothing to do with your Outlook rules.
Can emails be sent out normally if you disable all your Outlook rules?
And how did you add categories to those emails you would like to send out? Maybe this similar thread could help: Can't send delayed email immediately in outlook.

As I know, there might be several common factors which would cause similar issues, for example large attachments, corrupted datafiles or profiles and others. Please follow the steps in this article: Fix messages that are stuck in the Outbox and see if it could help.

If the issue still continues, I'm afraid there might be something wrong with your Outlook datafiles or profiles, so please try creating and using a new Outlook profile via Control Panel > Mail > Show profile and see if this issue could be resolved.

By the way, firewall and anti-virus program may also influence this issue, please remember to check them.

Hope this can be helpful.


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Hi @JeffYang-MSFT , Thank you for your prompt reply. I created a 2nd profile and tested the rule but have the same issue. I even deleted the rule and recreated it just to make sure there was nothing in the old rule stopping the exception emails. But the same issue exists. All regular messages (where the Category is not set) go out after one minute, as designed. The only issue is when I want to send the message immediately as an exception and set a Category. The message gets stuck in the Outbox folder and not even going after one minute like the regular emails. There are no attachments and it is a new profile. I don't think firewall and anti-virus programs are an issue nor any data corruption, as all regular emails are being sent after the one minute delay.

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Hi @PrakashGrama-5761,
Thanks for your reply here.
Just in case, I still would like to check how did you add categories to your sent emails? Do you take the same operations as the similar thread I mentioned above? Or via some other ways? If there is any difference, please feel free to let me know so that I can do the same tests in my Outlook.

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PrakashGrama-5761 answered PrakashGrama-5761 commented

Hi @JeffYang-MSFT , Yes, I am assigning categories the way you have said and my rule is also defined that way.

I tried 3 things: (a) created a new Category called "Send Immediately" (so that I don't use the color categories), set the rule to send immediately only when assigned to that category (b) changed the rule to send immediately if it is Yellow category and assigned a message to Yellow, (c) changed the rule to send it out if assigned to any category and set a category. In all cases, they get stuck. I can see the category in the Outbox and only the mail assigned with the category gets stuck.

I also tried another test where I set the exception category to Yellow and assigned a Blue category to see if it will go out after 1 min-delay (like all emails that are not assigned any category). And it got stuck!

Then I thought maybe my rule is blocking emails with any category and deleted the rule. Then I assigned a message with a category. And even that got stuck!! So the problem doesn't seem to be with the rule at all and instead is with a category being assigned to any email!

I have been restarting Outlook every time I changed the rule just to make sure it is applied but not rebooting.

I would appreciate it if you would test out sending an email with a category without any rules set and see if you can duplicate it. Any other thoughts?

Thanks for your help.

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I just now tested with a 2nd profile to confirm that it is not a profile corruption. But I have the same issue there. Even when I delete all Rules, mails don't go out once they are assigned a Category. So I don't think this is a Rules issue but more a Category issue for outgoing emails. Thanks

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JeffYang-MSFT answered JeffYang-MSFT edited

Hi @PrakashGrama-5761,

Thanks for your detailed reply.

Before going further, may I know what's the version of your Outlook? (File > Office Account > About Outlook). To avoid version-related issues, please make sure you have upgraded your Outlook to the latest version.
And what's the type of your account? POP, IMAP or Exchange?

I would appreciate it if you would test out sending an email with a category without any rules set and see if you can duplicate it.

I tried lots of tests in my Outlook 365 (Version 2008 Build 13127.21348) about, with or without rules, emails with category can all successfully been sent out normally, , as designed. Does this issue only happen to the specific email account on this specific Outlook client? In order to further confirm your issue, it is suggested for you to try the same tests for other personal email account and see if the issue has any difference.

By the way, personally I think repairing your Outlook program might be a necessary step about your issue.


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PrakashGrama-5761 answered

Hi @JeffYang-MSFT ,

My Outlook version is Microsoft Outlook for Microsoft 365 MSO (16.0.13801.20288) 64-bit. My Windows version is Windows 10 Enterprise 1909 OS Build 18363.1440 installed on 7/24/2020 on a HP Spectre Split 13x2 PC 13-m010dx running an Intel Core i7-8550U CPU @ 1.80 GHz 1.99 GHz and 16 GB RAM

I figured out that I am having this issue only on my desktop app and not online, where it works fine. On the desktop I tried all 4 combinations:

  1. Send with category and with rule

  2. Send without category with rule

  3. Send with category after deleting the rule

  4. Send without category after deleting the rule

The emails go out in case of #2 and #4 but get stuck in Outbox for #1 and #3. Hence I felt that the issue is not with the Rule but with the Category. I tried to Repair it but after a while it said something went wrong. I will run it again.

I asked my colleague to test it and it works fine for him with the Category from his desktop app. So it may be some corruption on my laptop? I have a spare laptop and will try it on that over the weekend.

Thanks,
Prakash

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PrakashGrama-5761 answered JeffYang-MSFT commented

Hi @JeffYang-MSFT

I tried to Repair but it ran into an error. Later I realized that it had uninstalled Office 365 from my laptop!! I reinstalled it from online. Now the rule works fine. All emails by default are delayed by a minute except when assigned a Category where it is sent immediately. Thanks for your help!

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Hi @PrakashGrama-5761,

Thanks for your updates.

Glad to see that this issue has been resolved. Congratulations!

By the way, in order to close this thread normally, please kindly accept helpful replies or your own reply as answers. Grateful to your understanding and support.

Have a nice day.


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Hi @JeffYang-MSFT , The problem has resurfaced now :-( It worked well after I uninstalled Office 365 and reinstalled it. So all emails go out after a one minute delay but when I assign a Category, the email gets stuck in Outbox. I could try the repair again but that may be a temporary solution. Any other thoughts? Any cache issues that could be triggering the rule to not work? Or any settings that need to be changed/deleted in command mode?

I deleted the rule and restarted Outlook. That was the only Rule I had and now there are no rules. The old email is still stuck in Outbox. I composed a new email after deleting all the rules and assigned it the same Category. Even that email is stuck. But when I test an email without a Category it goes out immediately as there is no delay set.

So looks like once the corruption happens, it stays. Hence I feel it may be some configuration being set somewhere. This happens only on the desktop app and not web version.

Thanks!

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Also, once a Category is assigned and it is in the Outbox, editing the email to remove all Categories has no affect. The email is still stuck even though it has no Category. So somewhere that flag, or an associated attribute, is not reset

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PrakashGrama-5761 answered JeffYang-MSFT edited

Hi @JeffYang-MSFT

I looked at the Troubleshooting options for Windows and don't see any topics related to Outlook other than a compatibility test. But this has been working well on Windows 10 for a long time and it doesn't seem to be a compatibility issue.

Where do I raise a ticket for a Windows 10 issue that is possibly corrupting Outlook outgoing mail with Category? As discussed, this is not a Rule issue as the mail gets stuck even when all rules are deleted and a Category is assigned to the outgoing email.

Once I hear from you, I will Accept Answer here to close the thread and open a new one there.

Thanks again for all your help!

Regards,
Prakash

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This morning I restarted my laptop and noticed that all the blocked emails in my Outlook outbox folder with a Category assigned were sent out! I tried to send another one but it got stuck. I then restarted my laptop again but the mail is still stuck in Outlook. Maybe it sends them out just once a week on Sundays :-) I have now put the date and time in the Subject as I cannot tell when I composed them. I don't restart my laptop daily but will try that the next few days.

I feel there is some local setting that is preventing it from being sent. Is it possible for me to delete some of the Outlook config files after I quit it and let it recreate those when I restart Outlook? I want to see if it sends them out then but gets corrupted soon after that. How can we explain the mails being sent out today?

Thanks,
Prakash

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Weird, honestly the first operation(create and use new Outlook profile) we did has already helped excluding most the factors from local Outlook settings. If possible, would you mind creating a new windows profile and test to see if the issue could be resolved there?

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Microsoft Q&A forum could also support issues about windows, if indeed necessary, you could just open a new thread and add some windows-related tags.

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